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craigslist

Vacation Rentals in Chicago

  1. Visiting the Evanston area for 3 days or more? Check us out.
    $269
    Evanston IL
  2. Marriott's Aruba Ocean Club (July 20, 2026 to July 27, 2026)
    $2,700
    Palm Beach Aruba
  3. Wyndham Glacier Canyon at The Wilderness Waterpar11/14-16 in 3 bdrm
    $695
    north chicagoland
  4. Condo - Bradenton Florida - Seasonal Rental
    $1,500
    Bradenton
  5. Old Naples Florida resort rental. Near Beach. Jan 10th thru Jan 17th
    $1,800
    Naples
  6. Waterfront Cottages with boats
    $135
    Barryton
  7. Perfect for groups
    $135
    Chicago, IL
  8. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $150
    Chicago, IL
  9. Perfect for groups
    $150
    Chicago, IL
  10. Ideally located in West Lakeview withing walking distance to Wrigley Field
    $150
    Chicago, IL
  11. Perfect for groups
    $150
    Chicago, IL
  12. JANUARY GETAWAY TO MEXICO
    $0
    Puerto Vallarta
  13. TOWNHOME FOR THANKSGIVING FAMILY GATHERING
    $0
    CHRISTMAS MOUNTAIN / WISCONSIN DELLS
  14. Modern Recent home
    $125
    Chicago
  15. Hotel rooms available discounted rates
    $0
    city of chicago
  16. Superbowl Party and Final Four Accommodations
    $1,990
    10 minutes from Grand Rapids Airport
  17. PUEBLO BONITO ROSE RESORT
    $4,000
    Chicago
  18. Condo in Chantecleer Lakes
    $1,200
    Naperville
  19. Gorgeous Top-floor 1 bed/1 bath
    $1,300
    Chicago
  20. New Years Eve and Independence Day week
    $800
    Wisconsin Dells, Wi.
  21. Perfect for groups
    $150
    Chicago, IL
  22. Condo on the beach
    $0
    7 Mile Beach
  23. Wisconsin Dells - Glacier Canyon Nov 20-22 w/10 waterpark wtbnds
    $299
    Wisconsin Dells
  24. Wisconsin Dells - Glacier Canyon Nov 23-25 w/ 4 wrtpk wristbands
    $249
    Wisconsin Dells
  25. Vacation / Temporary Furnished Luxury Rental Avail Jan and Feb 2026
    $8,500
    Libertvyille
  26. New construction elevator building
    $150
    Chicago, IL
  27. Perfect for groups
    $150
    Chicago, IL
  28. Escape Winter in Oceanfront Penthouse
    $3,995
    North Myrtle Beach
  29. Located in one of the most desired neighborhoods in Chicago
    $3,000
    Chicago
  30. Christie Lodge Timeshare Week for Sale (Avon near Vail) - $750
    $0
    Avon, CO.
  31. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 390
    $390
    Bartlett ILLINOIS 60103
  32. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  33. Furnished motel style suite, No Deposit daily $ 75.00 week;y 395.00
    $395
    Bartlett ILLINOIS 60103
  34. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 390
    $390
    Bartlett ILLINOIS 60103
  35. Furnished motel style suite, No Deposit daily $ 75.00 weekly $ 375
    $375
    Bartlett ILLINOIS 60103
  36. Furnished motel style suite, No Deposit daily $ 75.00 weekly $395
    $395
    Bartlett ILLINOIS 60103
  37. Wisconsin Dells - Glacier Canyon Dec 8-12 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  38. Wisconsin Dells - Glacier Canyon Dec 15-18 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  39. Wisconsin Dells - Glacier Canyon Dec 15-20 w/10 waterpark wtbnds
    $249
    Wisconsin Dells
  40. Perfect for large group
    $150
    Chicago
  41. Perfect for groups
    $135
    Chicago, IL
  42. Gold Coast Lake Michigan Corner Stidio
    $1,800
    Chicago
  43. Wisconsin Dells - Glacier Canyon Nov 20-22 w/8 waterpark wristbands
    $240
    Wisconsin Dells
  44. Modern and Well-Equipped Cabin in Minocqua, WI.
    $0
    Gurnee
  45. 5 STAR RESORT - GREAT Amenities + Full Kitchen
    $900
    WORLDWIDE
  46. 4 Bdrm Private Pool/Spa Home
    $4,000
    Palm Desert
  47. Wisconsin dells Glacier canyon
    $0
    Fredonia
  48. Smokey Mountain Fall vacatiion
    $850
    Gaitlinburg
  49. Attention snowmobilers
    $3,500
    Presque Isle
  50. rci points for sale
    $200
    fredonia
  51. Vacation home available for rent
    $3,195
    Chicago
  52. Assistance for right girl or couple
    $0
    city of chicago